Journal of the Chemical Society. Perkin transactions I p. 1673 - 1682 (1996)
Update date:2022-08-02
Topics:
Jackson, Richard F. W.
Briggs, Andrew D.
Brown, Paul A.
Clegg, William
Elsegood, Mark R. J.
Frampton, Christopher
Treatment of N-(toluene-p-sulfonyl)vinylsulfoximines 3 with methyllithium at -78°C, followed by addition of chlorotrimethylsilane, results in the efficient formation of α-silyl vinylsulfoximines 6 in good to excellent yield. Nucleophilic addition of a range of simple alkyl and aryl organometallics (lithium, copper-lithium and Grignard reagents) occurs in variable yield to give the Michael adducts 8 with organolithium reagents most effective. The degree of stereoselectivity of each of the addition reactions was determined by 1H NMR of the desilylated products 9, and proved to be synthetically useful for compounds in which the starting α-silylvinylsulfoximines were branched at the γ-position, and also when phenylhthium was used as the nucleophile. The sense of stereoselectivity was determined in two cases by X-ray crystal structure analyses (of 9e and 9i). A one-pot process for the conversion of α-silylvinylsulfoximines 6 to α-substituted carboxylic acids 11 was developed, using an in situ phenylselenation-oxidation process following the initial conjugate addition. Use of enantiomerically pure starting materials allowed the assignment of configuration of two carboxylic acids (13e and 13h) by comparison with literature data, and hence indirectly of the relative stereochemistry of the initial Michael adducts 9e and 9h.
View Morewebsite:http://www.shochem.com
Contact:021-50800795
Address:No.1043, Halei Rd, Zhangjiang Hi-Tech Park, Shanghai, Postcode 201203, China
Jinan Baozhao Pharmaceutical Co., Ltd
Contact:0086-531-86397156 82371858 82371868
Address:Huaneng Road, Jinan, Shandong ,China
Huaian Double Win Chemicals Co.,Ltd.
Contact:+86-13511538872
Address:Blk 43,Greenland Century Town,Huaian District, Huaian City,Jiangsu Province,China
website:http://www.sigmaaldrich.com
Contact:800 558-9160
Address:Industriestrasse 25CH-9471 Buchs SGSwitzerland
Suzhou Sibian Chemical Technology Co., Ltd
website:http://www.sibianpharm.com
Contact:+8618169181984,+8618013186906
Address:Room1404,BuildingA,Jiabao Square No.323 Baodai East Road,Wuzhong District,Suzhou Jiangsu China (215128)
Doi:10.1002/zaac.19966220819
(1996)Doi:10.1002/jccs.201600841
(2017)Doi:10.1016/0040-4039(96)01342-1
(1996)Doi:10.1016/0040-4039(96)01337-8
(1996)Doi:10.1021/om960509w
(1996)Doi:10.3390/molecules24020303
(2019)
